IVAS 2022 banner
IVES 9 IVES Conference Series 9 IVAS 9 IVAS 2022 9 Hemisynthesis, NMR Characterization and UHPLC-Q-Orbitrap /MS² identification of (+)-Catechin oxidation products in red wines and grape seed extracts

Hemisynthesis, NMR Characterization and UHPLC-Q-Orbitrap /MS² identification of (+)-Catechin oxidation products in red wines and grape seed extracts

Abstract

(+)-Catechin—laccase oxidation dimeric standards were hemi-synthesized using laccase from Trametes versicolor in a water-ethanol solution at pH 3.6. Eight fractions corresponding to eight potential oxidation dimeric products were detected. The fractions profiles were compared with profiles obtained with two other oxidoreductases: polyphenoloxidase extracted from grapes and laccase from Botrytis cinerea. The profiles were very similar, although some minor differences suggested possible dissimilarities in the reactivity of these enzymes. Five fractions were then isolated and analyzed by 1D and 2D NMR spectroscopy. The addition of traces of cadmium nitrate in the samples solubilized in acetone-d6 led to fully resolved NMR signals of phenolic protons, allowing the unambiguous structural determination of six reaction products, one of the fractions containing two enantiomers. These products were then analyzed in grape seed extracts and red wines (UHPLC-Q-Orbitrap MS). The different dimers had different fragmentation patterns according to their interflavan linkage position. Oxidation dimeric compounds had a specific fragment ion at m/z 393, missing for B-Type dimers fragmentations. A fragment ion at m/z 291 occurred and was specific for oxidation dimeric compounds with a C-O-C linkage. Higher level oxidation products had abundant specific fragments: m/z 425, 397 and 245. These fragmentations were useful to identify them in complex samples such as grape seed extracts and wines. Three grape varieties and three ripening stages were selected and the corresponding seed extracts were obtained. The analyses revealed an increasing trend for the oxidation markers during grape ripening. The analysis of Syrah wines (2018, 2014, 2010) showed a decreasing trend of these molecules during wine ageing which might be due to further oxidation.

DOI:

Publication date: June 23, 2022

Issue: IVAS 2022

Type: Article

Authors

Saucier Cedric1, Deshaies Stacy1, Le Guernevé Christine1,2, Sommerer Nicolas1,2, Garcia Lucas Suc François1, Mouls Laetitia1

1SPO, Université de Montpellier, INRAE, Institut Agro, UMR SPO, Faculté de Pharmacie, 15 avenue Charles Flahault, 34000 Montpellier, France
2INRAE, PROBE Research Infrastructure, PFP Polyphenol Facility, 34060 Montpellier, France

Contact the author

Keywords

wine, grape, polyphenol,oxidation, catechin

Tags

IVAS 2022 | IVES Conference Series

Citation

Related articles…

Measurements of the oxygen dissolved in white wines elaborated in barrels without to open the bung of the barrels

Bases on oxoluminescence, we have developed an innovative device for measuring dissolved oxygen in wines in barrels without opening the bung. This system is directly inserted into the wood during the barrel elaboration and can be positioned at different locations of the barrel (the head, the hull …). During two successive vintages we have used this device notably to follow the oxygen dissolved of whites wines elaborated in barrels. This allowed us initially to monitor the oxygen levels of the harvest to bottling the whole elaboration process in barrels of white wines without using techniques of measurement suitable to modify the real values in wines (opening the bung to plunge an oximeter).

Transforming winemaking waste: grape pomace as a sustainable source of bioactive compounds

Grapevines (Vitis vinifera L.) are plants of great economic importance, with over 80% of grape production dedicated to wine production, yielding more than 258 million hectoliters annually [1].

Hierarchy of the interactions between physical and biological parameters intervening in the Pyrenean Gascon foothill vineyard

Un travail sur les A.O.C. du piémont pyrénéen occidental permet de construire une hiérarchie de paramètres climatiques, géo-pédologiques, morphologiques, de saisir leurs niveaux d’interaction et d’élaborer une méthodologie pour proposer un zonage

Correspondence between physiological plant variables and carbon isotope composition in different climate winegrape regions

The climate is the environmental factor that contributes with greater weight in the variability of the yield and the composition of the grape, therefore, it is key in the determination of the typicity of the product. Of the environmental factors, the evolution of water availability conditions, among other things, the biochemical evolution of the compounds of the grape and the type of wine to be elaborated. An integrating parameter of the hydric state of the plant is the carbon isotopic composition (δ13C). This indicator is a useful parameter to characterize the water status during the maturation period and estimate the transpiration efficiency or water use efficiency (EUA) in the vine.

May lactic acid bacteria play an important role in sparkling wine elaboration?

The elaboration of sparkling wine is a demanding process requiring technical as well as scientific skills. Uncovering the role of the terroir to the final product quality is of great importance for the wine market. Although the impact of the yeast strains and their metabolites on the final product quality is well documented, the action of bacteria still remains unknown. The malolactic fermentation (MLF) is carried out by the lactic acid bacteria after the alcoholic fermentation in order to ensure the microbial stability during the second fermentation that takes place in the bottle or in tanks. Oenococcus oeni is the only selected species to drive MLF that has been commercialized for sparkling wine elaboration and it is naturally present on grapes, in the cellar and also in the final product. However, whether the bacterial strain contributes to the sensory characteristics of sparkling wine is still questioned.